Synthesis of carbohydrate-centered oligosaccharide mimetics equipped with a functionalized tether

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5275-5281

  Dubber, Michael ^a   Lindhorst, Thisbe K ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; GLUCOSE; GLYCOCONJUGATE; MANNOSIDE; MONOSACCHARIDE; OLIGOSACCHARIDE; TREHALOSE;

AFFINITY CHROMATOGRAPHY; ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE METABOLISM; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; GLYCOSYLATION; REACTION ANALYSIS;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR MIMICRY; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TREHALOSE;

EID: 0034714566     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000432s     Document Type: Article

References (32)

1. Varki, A. Glycobiology 1993, 3, 97.
2. Dwek, R. A. Chem. Rev. 1996, 96, 683.
3. Kahane, I.; Ofek, I. Toward Anti-Adhesion Therapy for Microbial Diseases. Adv. Exp. Med. Biol. 1996, 408.
4. Bovin, N. V.; Gabius, H.-J. Chem. Soc. Rev. 1995, 413.
5. Simanek, E. E.; McGarvey, G. J.; Jablonski, J. A.; Wong, C.-H. Chem. Rev. 1998, 98, 833.
6. Jayaraman, N.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1193.
7. Lindhorst, Th. K.; Dubber, M.; Krallmann-Wenzel, U.; Ehlers, S. Eur. J. Org. Chem. 2000, 2027.
8. Wijsman, E. R; Filippov, D.; Valentijn, A. R. P. M.; van der Marel, G. A.; van Boom, J. H. Red. Trav. Chim. Pays-Bas 1996, 115, 397.
9. Wong, C.-H.; Ye, X.-S.; Zhang, Z J. Am. Chem. Soc. 1998, 120, 7137.
10. Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem. 1998, 110, 2620; Angew. Chem., Int. Ed. 1998, 37, 2503.
11. Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem. 1998, 110, 2620; Angew. Chem., Int. Ed. 1998, 37, 2503.
12. Kitov, P. I.; Sadowska, J. M.; Mulvey, G.; Armstrong, G. D.; Ling, H.; Pannu, N. S.; Read, R. J.; Bundle, D. R. Nature 2000, 403, 669.
13. Kieburg, C.; Dubber, M.; Lindhorst, Th. K. Synlett 1997, 1447.
14. Buskas, T.; Söderberg, E.; Konradsson, P.; Fraser-Reid, B. J. Org. Chem. 2000, 65, 958.
15. Lindhorst, Th. K.; Kieburg, C.; Krallmann-Wenzel, U. Glycoconjugate J. 1998, 15, 605.
16. Kötter, S.; Krallmann-Wenzel, U.; Ehlers, S.; Lindhorst, Th. K. J. Chem. Soc., Perkin Trans. 1 1998, 2193.
17. Takano, T.; Nakatsubo, F.; Murakami, K. Carbohydr. Res. 1990, 203, 341.
18. Nouguier, R.; Mchich, M. J. Org. Chem. 1985, 50, 3296.
19. Dubber, M.; Lindhorst, Th. K. Carbohydr. Res. 1998, 310, 35.
20. Brown, H. C.; Chen, J. C. J. Org. Chem. 1981, 46, 3978.
21. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
22. Wulff, G.; Röhle G. Angew. Chem. 1974, 86, 173; Angew. Chem., Int. Ed. Engl. 1974, 13, 157.
23. Wulff, G.; Röhle G. Angew. Chem. 1974, 86, 173; Angew. Chem., Int. Ed. Engl. 1974, 13, 157.
24. Bien, F.; Ziegler, T. Tetrahedron: Asymmetry 1998, 9, 781.
25. See the Supporting Information.
26. Nukada, T.; Berces, A.; Whitfield, D. M. J. Org. Chem. 1999, 64, 9030.
27. Harvey, D. J.; Küster, B.; Naven, T. J. P. Glycoconjugate J. 1998, 15, 333.
28. Wang, J.; Sporns, P.; Low, N. H. J. Agric. Food Chem. 1999, 47, 1547.
29. Nonami, H.; Tanaka, K; Fukuyama, Y.; Erra-Balsells, R. Rapid Commun. Mass Spectrom. 1998, 12, 285.
30. McReynolds, K. D.; Hadd, M. J.; Gervay-Hague J. Bioconjugate Chem. 1999, 10, 1021.
31. Weatherman, R. V.; Kiessling, L. L. J. Org. Chem. 1996, 61, 534.
32. Cao, S.; Tropper, F. D.; Roy, R. Tetrahedron 1995, 51, 6679.